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Trendy Shoes to Flex All Season Long

Hot Picks for Your Main Character Moment

Step into your spotlight with trendy shoes that make every outfit pop. From sun-soaked hangs to formal soirées, Windsor’s shoe collection is stacked with heels, sandals, boots, booties, and more—basically, every style you need to go from “getting ready” to “it girl energy” in a snap. Whether you’re that always-put-together friend, the spontaneous social butterfly, or somewhere in between, your next obsession starts here.

Dress Heels That *Do the Most*

This season’s edit? Total main character. Lace-up heels with 3D butterfly and flower details bring flirty vibes, while rhinestone-covered stilettos turn heads from every angle. For weddings or big event energy, dress heels in metallic finishes and platforms with trendy hardware give instant glam. Bridesmaid heels and wedding dress shoes stun in sleek satins, mesh, or glittery faux leather—and they’re all made with Windsor’s comfort-first insoles so your feet feel as good as you look.

Everyday Shoes with Main-Character Energy

On casual days, keep your cool in mules, flats, or low-block heels that go with everything from joggers to jean shorts. Into a bold boot moment year-round? We got you. Knee-high boots, cowgirl boots, and lug sole boots bring that unexpected edge to your festival ‘fit or rooftop vibe. And yes, they come in everything from classic neutrals to dopamine-bright colors made for selfies.

The Details That Make a Difference

With almond, square, pointy, peep toe, and open-toe styles, there’s a toe shape for every mood. Adjustable straps, metallic sheens, and textures like patent faux leather and all-over rhinestones make it easy to build your look from the feet up. And because we know you’ve got places to be (and pics to post), most styles come in multiple heel heights so you can slay your day—comfortably.

Trendy Shoes = Your New Flex

Scroll less and slay more with Windsor’s must-have shoes. These trendy shoes are ready to upgrade your rotation, one click, tap, or store trip at a time.

What Shoes Can I Wear With Jeans?

Honestly? Anything from Windsor. Pair your straight-leg denim with block heels or heeled mules for that low-effort, high-style vibe. Craving something cooler for cropped jeans? Try pointed-toe stilettos or trendy neutral-toned booties to elevate your look.

For casual slays, strappy sandals or flats are perfect for brunch or running errands with style. Want to dress up your fav dark-wash jeans? Go for a glitter heel, bold platform, or clear mule—you’ll be out the door and dressed to impress in seconds.

What Shoes Can I Wear With Jeans?

The best shoes to wear with jeans depend on your denim style, wash, and overall look. Black ankle boots or heeled mules pair effortlessly with straight-leg jeans for a sleek, polished vibe. For cropped denim, opt for pointed-toe heels, strappy mules, or neutral-toned boots to elevate your outfit for work or date night.

Keeping it casual? A stylish yet comfortable sandal adds an effortless edge to your everyday look. If you're dressing up dark-wash jeans with a bustier or statement-sleeve top, go for trendy clear mules or block heels that are easy to wear for hours.

  • Moving On Faux Leather Lucite Booties

    Move on from basic to chic in booties that elevate your looks! The booties feature an around the ankle fit, an inner zipper closure, a pointed toe, and a narrow lucite block heel. Complete your look with high waist jeans and an oversized sweater. 

    Fit & Features

    • Around the ankle fit
    • Inner zipper closure
    • Pointed toe
    • Narrow lucite block heel
    • Faux leather material

    Style Number/Barcode: 07403-0311

    Category Name: Women’s Shoes

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clearly Chic Lucite Block Heels

    Clearly stay on trend in heels that keep your looks stylish and chic. The heels feature an adjustable ankle strap, an open almond toe with clear strap, and a lucite block heel. Complete your look with a chic sweater dress and duster earrings. 

    Fit & Features 

    • Adjustable clear ankle strap
    • Clear strap at the heel
    • Open almond toe with clear strap
    • Lucite block heel
    • Faux patent leather sole

    Style Number/Barcode: 07401-2388

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Classic Block Heels

    Sometimes you just have to keep it classic with a good pair of block heels! These feature an open almond toe and a shorter block heel. Pair with your fave paper bag pants and a chic blouse for a look you can totally wear to the office.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Adjustable around the ankle strap
    • Open back
    • Short block heel
    • Faux nubuck

    Style Number/Barcode: 07401-2383

    Category Name: Women’s Shoes

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spin Me Around Spiral Rhinestone Stiletto Heels

    Give it a twirl in rhinestones! These heels make a true shining statement and we are obsessed. They feature a rhinestone adorned spiral wrap around ankle strap. Style with a mini dress and let those legs shine!

    Fit & Features

    • Open almond toe
    • Double band detail
    • Spiral wrap around ankle strap
    • Rhinestone detailing
    • Shiny faux leather with a metallic finish
    • Skinny stiletto heel

    Style Number/Barcode: 07401-2306

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Chic Rhinestone Bow Heels

    Show off your cute and chic side in these adorable rhinestone bow heels! Glam it up in these shoes that feature a statement rhinestone bow and a sleek stiletto heel. Get ready to grab drinks with your girls in these sweet heels and a stunning little black dress.

    Fit & Features

    • Open toe
    • Rhinestone embellished bow accent
    • Adjustable around the ankle strap
    • Closed-back
    • Stiletto heel
    • Patent PU material

    Style Number/Barcode: 07401-2210

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Dance Peep Toe Clear Heels

    These peep toe clear heels are ready for you to dance in and make a statement! These heels have a fun and sexy element with their rhinestone wrap around ankle strap that will really amp up your special event dress. Pair with a sparkly clutch to bring the glamour.

    Fit & Features

    • Peep toe
    • Curved band over the toe
    • Clear heel backing 
    • Chrome lining and on the heel
    • Rhinestone detailing
    • Adjustable pin-buckle closure

    Style Number/Barcode: 07401-2312

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay Each Step Block Heels

    You'll slay each step in these adorable faux nubuck block heels! They feature a criss cross ankle strap design and a shorter sturdy block heel. A must-have for wearing from the office to dinner, pair with a chic curve-hugging pencil skirt and a flowy blouse.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Criss cross front design
    • Adjustable ankle strap
    • Closed-back
    • Short block heel
    • Faux nubuck material

    Style Number/Barcode: 07401-2387

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chic Quilted Faux Leather Sneakers

    Get a casual chic vibe in these adorable faux leather slip-on sneaks! They feature a quilted diamond faux leather design and a thick sole. Pair with a cute mini dress and layer on a denim jacket for a date night with bae.

    Fit & Features

    • Slip-on design
    • Elastic details
    • Quilted diamond design
    • PU material
    • Stud detailing on the back
    • Thick sole

    Style Number/Barcode: 07407-0168

    Category Name: Women’s Shoes

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feelin' Wild Leopard Print Sneakers

    Showcase your sassy, wild side in these too cute leopard print sneaks! They feature an easy slip-on design with a thick sole. Pair with some mom jeans and a graphic tee to go shopping with your squad.

    Fit & Features

    • Slip-on design
    • Elastic details
    • Leopard print
    • Thick sole

    Style Number/Barcode: 07407-0167

    Category Name: Women’s Shoes

    Price: $14.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Touch Of Glam Block Heels

    Add just a touch of glam to your 'fit with these metallic block heels! These feature an open almond toe and a shorter block heel. Pair with your fave little black dress to make a gorgeous statement.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Adjustable around the ankle strap
    • Open back
    • Short block heel
    • Metallic finish

    Style Number/Barcode: 07401-2385

    Category Name: Women’s Shoes

    Price: $14.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace Up Peep Toe Stiletto Booties

    Lace-up in these booties that elevate your looks this season! They feature a zippered back, a cutout lace-up front, peep toe, and a sleek stiletto heel. Complete your look with high waist pants and a chunky cable knit sweater. 

    Fit & Features

    • Ankle-length 
    • Zippered back  
    • Cutout lace-up front 
    • Peep toe
    • Stiletto heel
    • Faux suede material 

    Style Number/Barcode: 07403-0342

    Category Name: Women’s Shoes

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Zip-Up Block Heels

    Keep it basic with a classic zip-up block heel! These feature an open almond toe, a thin ankle strap, and will go with all of your 'fits. Keep it casual with a pair of skinny jeans for a lunch date, or dress it up with a bodycon dress for a night out.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Thin ankle strap
    • Closed-back with a zipper
    • Sturdy block heel

    Style Number/Barcode: 07401-2390

    Category Name: Women’s Shoes

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step It Up Faux Leather Wedge Sneakers

    Step up your shoe game with these trendy faux leather wedge sneaks! They feature a lace-up front, side zipper detail, and a wedge heel. Amp up your shopping day by pairing these sneakers with a mini dress and hoop earrings.

    Fit & Features

    • Lace-up front
    • Side zipper detail
    • Wedge heel
    • PU material

    Style Number/Barcode: 07407-0159

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chrome Cutie Rhinestone Block Heels

    Reflect glamour in these block heels that bring the glitz to your formal outfits! Impress at your special event in chrome heels that features a dazzling rhinestone embellished strap and a trendy block heel to strut with confidence. Complete your look with a statement skater dress! 

    Fit & Features

    • Closed-back
    • Adjustable ankle strap 
    • Open almond toe
    • Rhinestone embellished strap over the toe
    • Block heel
    • Chrome finish 

    Style Number/Barcode: 07401-2213

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Thing Block Heel Booties

    Keep it fierce in booties that showcase your wild side! The booties feature an around the ankle length, a pointy toe, a stacked block heel, and a textured faux leather body. Complete your look with high waist jeans and an oversized cardigan this season! 

    Fit & Features

    • Around the ankle-length 
    • Pull-tabs at the back 
    • Pointy toe
    • Inner-zipper closure
    • Stacked block heel
    • Textured faux leather material 

    Style Number/Barcode: 07403-0312

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Straps Lace-Up Block Heels

    Lace-up in trendy block heels this season! Perfect for that upcoming weekend getaway or date night, these heels feature lace-up straps, a narrow block heel, and composed of faux suede material. Complete your look with a stunning floral dress and fringe earrings!

    Fit & Features

    • Open back
    • Lace-up straps
    • Criss-cross straps over the toe 
    • Clear strap over the toe
    • Narrow block heel
    • Open square toe
    • Faux suede material 

     

    Please be advised that these heels run 1/2 a size small.

    Style Number/Barcode: 07401-2323

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Under The Sun Straw Buckle Slide Sandals

    A pair of straw buckle strap sandals you'll reach for every sun shining day!

    Fit & Features

    • Round toe
    • Dual straw buckle straps
    • Comfortable footbed
    • Traction bottom
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1290

    Category Name: Women’s Shoes

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Cute Slip On Sneakers

    Keep it casual in sneakers to nail down those low-key outfits this season. The sneakers feature an easy slip-on design, a round toe, and a canvas material body. Complete your effortlessly casual look with a graphic tee and high waist jeans. 

    Fit & Features

    • Slip-on design
    • Round toe
    • Canvas material body
    • Thick sole
    • Available in beige, black and camo print  

     

    Please be advised that these shoes run 1/2 a size small.

    Style Number/Barcode: 07407-0064

    Category Name: Women’s Shoes

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Strappy Faux Suede Block Heels

    Strap up in stunning block heels that elevate your looks! Perfect for that upcoming bridal shower or date night, these heels feature lace-up straps, a narrow block heel, and composed of faux suede material. Complete your look with a stunning floral dress and fringe earrings!

    Fit & Features

    • Open back
    • Lace-up straps
    • Criss-cross straps over the toe 
    • Clear strap over the toe
    • Narrow block heel
    • Open square toe
    • Faux suede material 

     

    Please be advised that these heels run 1/2 a size small.

    Style Number/Barcode: 07401-2324

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Style Block Heel

    Wrap yourself in these chic block heels to all your favorite looks! Perfect for stepping out for a casual brunch, these heels feature a wrap-around strap that sits at the mid-calf, criss-cross straps over the toe and a low block heel. Complete your look with a trendy sundress.

    Fit & Features

    • Wrap-around straps
    • Open back
    • Open almond-toe
    • Crisscross straps over the toe
    • Low block heel 

    Style Number/Barcode: 07401-2371

    Category Name: Women’s Shoes

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nubuck Basic Short Block Heels

    These basic short block heels are a must-have for any wardrobe! They will complete your work from home ensemble with their sturdy block heel and sleek nubuck material. Pair with your fave blouse and curve hugging pencil skirt to further level up your look!

    Fit & Features

    • Open almond toe | Toe strap
    • Around the ankle thin strap
    • Closed back | Zipper closure
    • Sturdy short block heel
    • Nubuck material

    Style Number/Barcode: 07401-0976

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Nubuck Peep Toe Stiletto Heels

    These stilettos will elevate your whole 'fit! Have a fancy dinner in with these heels that feature a peep toe and nubuck material. Pair with a curve hugging midi dress and some adorable stud earrings for a beyond gorgeous look.

    Fit & Features

    • Almond peep toe
    • Closed back
    • Stiletto heel
    • Nubuck material

    Style Number/Barcode: 07401-2378

    Category Name: Women’s Shoes

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keepin' It Simple Double Band Mules

    Keep it simple and timeless when you slip into these effortless mules! Pair with cut off denim, or a simple work wear outfit!

    • Open almond toe
    • Double thick bands
    • Slide on fit
    • Block heel
    • Faux nubuck

    Style Number/Barcode: 07401-0927

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strut It Out Caged Strappy Heels

    Strut it out with confidence in a pair of caged strappy heels! Style them perfectly with high waist black denim, or a flowing maxi dress!

    • Open almond toe
    • Braided caged design
    • Ankle strap
    • Stacked heel
    • Adjustable pin buckle closure

    Style Number/Barcode: 07403-0300

    Category Name: Women’s Shoes

    Price: $18.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale